US3455983A - Halogen substituted hydroxy-benzaldehyde hydrazonium salts - Google Patents

Halogen substituted hydroxy-benzaldehyde hydrazonium salts Download PDF

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Publication number
US3455983A
US3455983A US512198A US3455983DA US3455983A US 3455983 A US3455983 A US 3455983A US 512198 A US512198 A US 512198A US 3455983D A US3455983D A US 3455983DA US 3455983 A US3455983 A US 3455983A
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United States
Prior art keywords
benzaldehyde
hydrazonium
halogen substituted
parts
salts
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Expired - Lifetime
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US512198A
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English (en)
Inventor
Erwin Nikles
Otto Rohr
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BASF Schweiz AG
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Ciba AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/30—Nitrogen atoms non-acylated

Definitions

  • the present invention provides new hydrazonium salts wherein R represents a phenyl radical containing a hy-'" droxyl group and one, two or three halogen atoms, and R R and R are identical or different lower aliphatic radicals of which two together may form a ring of 5 or 6 members, if desired through a hetero atom, and X represents an anion.
  • lower aliphatic radicals are, for example, lower alkyl, alkenyl, alkinyl, halogenalkyl, halogenalkenyl or halogenalkinyl radicals.
  • the new hydrazonium salts of the above formula possess valuable biocidal properties, for example, they are potent herbicides and may also be used as defoliating agents.
  • the symbol X may, for example, represent a halogen atom, an alkylsulphonyloxy residue or the unilaterally esterified sulphuric acid residue.
  • the reaction may be carried out in the presence or absence of a solvent.
  • Suitable solvents are, for example, methanol, ethanol, acetone, acetohitrile, benzene or toluene.
  • the present invention also provides herbicidal preparations as well as preparations for defolating plants, comprising as active ingredient a compound of the formula where R represents a phenyl radical containing a hydroxyl group and one, two or three halogen atoms, and R R and R are identical or different lower aliphatic radicals of which two together may form a ring of 5 or 6 members, if desired through a hetero atom, and X represents an anion, together with a suitable carrier.
  • the preparation may also contain one or more of the following additives: a vehicle, a solvent, a dispersant, a wetting agent, an adhesive, a fertilizer and further pesticides.
  • the products mentioned above are especially suitable for controlling undesired plant growth and for defolating 'or desiccating plants, for example, tomatoes, cotton or the like.
  • hydrazonium salts of the Formula I are water-soluble, they are extremely simple to apply. In most cases, they may be sprayed in the form of aqueous solutions. Frequently, especially when a long contact period is desired, they may also be applied in the form of solutions or suspensions in organic solvents. Many hydrazonium salts of the Formula I are only sparingly soluble in water; they are formulated by the usual methods. They may be applied in the form of wettable powders, granulates, pellets, emulsifiable oil concentrates or aqueous dispersions.
  • assolid vehicles for the manufacture of dusting and casting preparations there may be used assolid vehicles: talcum, kaolin, bentonite, calcium carbonate, calcium phosphate, or coal, cork meal, wood meal or -other materials of vegetable origin. It is also very advantageous to manufacture granulated preparations.
  • the different forms of application may incorporate the usual additives for improving the distribution, the adhesion, the stability towards rain or the penetration. As such substances, there may be mentioned fatty acids, resin, glue, casein and alginates.
  • the proportion of vehicle used may vary within wide limits, for example from 10 to 98%, referred to the weight of the preparation as a whole.
  • the herbicidal products of this invention advantageously contain a surface-active agent, for example an emulsifier, a wetting agent or a dispersant to facilitate the dispersion of the product in water.
  • Suitable surface-active agents may be of the cationic, anionic or nonionic kind; mixtures of two or more such agents are likewise suitable.
  • wetting agents that can be incorporated in the preparations of this invention, there are preferably used for example, alkyl and alkyl-aryl polyether alcohols, polyoxyethylene sorbitol or sorbitan fatty acid esters, polyethylene glycol fatty acid esters and fatty acid alkylolamides.
  • the present invention also includes a method of controlling undesired plant growth which comprises applying to a crop area the preparations of the invention as hereinbefore defined.
  • the products of this invention may be used as such or in admixture or conjunction with conventional herbicides and/ or defoliants.
  • the precipitated product is filtered off, washed with toluene and dried under vacuum; it can be crystallized from alcohol and melts and decomposes at 175 to 180 C.
  • N ,N-pentamethylene-hydrazonium iodide 74.8 parts of 3,5-diiodo-4-hydroxy-benzaldehyde are condensed at room temperature in 500 parts by volume 75 of methanol with 20 parts of N-aminopiperidine. The reaction is accompanied by a slight evolution of heat. After 1 hour, the solution of the product is evaporated and the residue crystallized from cyclohexane; it melts at 118 to 119 C.
  • EXAMPLE 4 The compound obtained in Example 1 was turned into a wettable powder iin the following manner:
  • Example 6 The compound obtained in Example 2(a) is turned into an emulsifiable, herbicidal oil concentrate as follows:
  • the resulting concentrate can be diluted with water in any desired proportion, for example to a concentration of 6, 4 or 2% of active ingredient.
  • EXAMPLE 7 The compounds of Examples 1(a) and 2(a) were formulated as described in Example 5.
  • Hydrazonium salts of the general formula 3 The compound of the formula References Cited UNITED STATES PATENTS 7/1965 Harvey 260-566 OTHER REFERENCES Smith et al. (I), (DA. volume 52 pp. 1096-1097 (1957).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US512198A 1964-12-18 1965-12-07 Halogen substituted hydroxy-benzaldehyde hydrazonium salts Expired - Lifetime US3455983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1635864A CH476457A (de) 1964-12-18 1964-12-18 Herbizides Mittel

Publications (1)

Publication Number Publication Date
US3455983A true US3455983A (en) 1969-07-15

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ID=4416650

Family Applications (1)

Application Number Title Priority Date Filing Date
US512198A Expired - Lifetime US3455983A (en) 1964-12-18 1965-12-07 Halogen substituted hydroxy-benzaldehyde hydrazonium salts

Country Status (7)

Country Link
US (1) US3455983A (de)
BE (1) BE673984A (de)
CH (1) CH476457A (de)
DE (1) DE1518689A1 (de)
FR (1) FR1479263A (de)
GB (1) GB1126035A (de)
NL (1) NL6516506A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864349A (en) * 1970-06-11 1975-02-04 Fujisawa Pharmaceutical Co Hydrazonium Salts

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3197504A (en) * 1961-02-16 1965-07-27 Du Pont Chlorobenzaldehyde hydrazones and their hydrazonium salts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3197504A (en) * 1961-02-16 1965-07-27 Du Pont Chlorobenzaldehyde hydrazones and their hydrazonium salts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864349A (en) * 1970-06-11 1975-02-04 Fujisawa Pharmaceutical Co Hydrazonium Salts

Also Published As

Publication number Publication date
DE1518689A1 (de) 1969-08-14
BE673984A (de) 1966-06-17
FR1479263A (fr) 1967-05-05
NL6516506A (de) 1966-06-20
GB1126035A (en) 1968-09-05
CH476457A (de) 1969-08-15

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